# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Copper(I)_tricyanomethanide_acetonitrile
_audit_creation_date             14-07-16
_audit_creation_method           CRYSTALS_ver_14.40

_oxford_structure_analysis_title 
'Acetonitrilocopper(I) tricyanomethanide in Pbca'
_chemical_name_systematic        'Acetonitrilocopper(I) tricyanomethanide'


_exptl_special_details           
; 
 The crystal was 
placed in the cold stream of an Oxford 
Cryosystems open-flow nitrogen cryostat (Cosier & 
Glazer, 1986) with a nominal stability of 0.1K. 
 
Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. 
;


#end of refcif 
_cell_length_a                   12.9802(3)
_cell_length_b                   8.14490(18)
_cell_length_c                   14.5848(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1541.94(5)

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a '
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
-x+1/2,y+1/2,z
x+1/2,-y+1/2,-z
x,-y+1/2,z+1/2
-x,y+1/2,-z+1/2
-x+1/2,-y,z+1/2
x+1/2,y,-z+1/2

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cu -1.9646 0.5888 13.3380 3.5828 7.1676 0.2470 5.6158 11.3966 1.6735 64.8126
1.1910 'International Tables Vol C 4.2.6.8 and 6.1.1.4'


_cell_formula_units_Z            8

# Given Formula = C6 H3 Cu1 N4 
# Dc =      1.68 Fooo =    768.00 Mu =     34.78 M =    194.66
# Found Formula = C6 H3 Cu1 N4 
# Dc =      1.68 FOOO =    768.00 Mu =     34.78 M =    194.66

_chemical_formula_sum            'C6 H3 Cu1 N4'
_chemical_formula_moiety         'C6 H3 Cu1 N4'
_chemical_compound_source        
'Reagents obtained from Sigma Aldrich and Alfa Aesar'
_chemical_formula_weight         194.66


_cell_measurement_reflns_used    6465
_cell_measurement_theta_min      6
_cell_measurement_theta_max      77
_cell_measurement_temperature    100

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.033
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_max          0.039

_exptl_crystal_density_diffrn    1.677
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
# Non-dispersive F(000): 
_exptl_crystal_F_000             768
_exptl_absorpt_coefficient_mu    3.478

# Sheldrick geometric approximatio 0.89 0.89 
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
; 
 Analytical Absorption (De Meulenaer & Tompa, 1965) 
;
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_T_max  0.89
_diffrn_measurement_device_type  'Oxford Diffraction SuperNova'
_diffrn_measurement_device       Area
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_method       'φ & ω scans'

# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection       'SuperNova, (Oxford Diffraction, 2010)'
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'

_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_number         0
_diffrn_standards_decay_%        ?

_diffrn_ambient_temperature      100
_diffrn_reflns_number            14516
_reflns_number_total             1620
_diffrn_reflns_av_R_equivalents  0.025
# Number of reflections without Friedels Law is 0 
# Number of reflections with Friedels Law is 1620 
# Theoretical number of reflections is about 3247 


_diffrn_reflns_theta_min         6.068
_diffrn_reflns_theta_max         76.661
_diffrn_measured_fraction_theta_max 0.996

_diffrn_reflns_theta_full        76.661
_diffrn_measured_fraction_theta_full 0.996


_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_reflns_limit_h_min              0
_reflns_limit_h_max              16
_reflns_limit_k_min              0
_reflns_limit_k_max              10
_reflns_limit_l_min              0
_reflns_limit_l_max              18

_oxford_diffrn_Wilson_B_factor   1.27
_oxford_diffrn_Wilson_scale      0.11

_atom_sites_solution_primary     direct
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens   difmap

_refine_diff_density_min         -0.29
_refine_diff_density_max         0.26


# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 


# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_refine_ls_number_reflns         1620
_refine_ls_number_restraints     0
_refine_ls_number_parameters     100
_oxford_refine_ls_R_factor_ref   0.0229
_refine_ls_wR_factor_ref         0.0542
_refine_ls_goodness_of_fit_ref   0.9951
_refine_ls_shift/su_max          0.0020665
_refine_ls_shift/su_mean         0.0000816


# The values computed with all filters except I/sigma 
_oxford_reflns_number_all        1620
_refine_ls_R_factor_all          0.0229
_refine_ls_wR_factor_all         0.0542

# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression     I>2.0σ(I)
_reflns_number_gt                1480
_refine_ls_R_factor_gt           0.0199
_refine_ls_wR_factor_gt          0.0524

# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration .


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_hydrogen_treatment    constr #undef, noref, refall,
# refxyz, refU, constr or mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.03P)² + 0.49P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atoms attached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
Cu1 Cu 0.588127(13) 0.44049(2) 0.628675(12) 0.0136 1.0000 Uani . . . . . .
C11 C 0.69527(9) 0.32962(15) 0.81154(8) 0.0159 1.0000 Uani . . . . . .
C12 C 0.86036(9) 0.32301(15) 0.88643(8) 0.0148 1.0000 Uani . . . . . .
C13 C 0.70950(9) 0.20812(15) 0.96428(8) 0.0141 1.0000 Uani . . . . . .
C14 C 0.75490(9) 0.28398(16) 0.88784(8) 0.0151 1.0000 Uani . . . . . .
C21 C 0.59224(10) 0.82529(18) 0.64049(9) 0.0210 1.0000 Uani . . . . . .
C22 C 0.59681(13) 1.00325(18) 0.65007(12) 0.0312 1.0000 Uani . . . . . .
N11 N 0.64984(8) 0.36967(15) 0.74738(7) 0.0193 1.0000 Uani . . . . . .
N12 N 0.94616(8) 0.35831(15) 0.88161(7) 0.0176 1.0000 Uani . . . . . .
N13 N 0.67102(8) 0.14601(14) 1.02642(7) 0.0169 1.0000 Uani . . . . . .
N21 N 0.58913(9) 0.68611(16) 0.63311(8) 0.0212 1.0000 Uani . . . . . .
H221 H 0.5567 1.0371 0.7002 0.0491 1.0000 Uiso R . . . . .
H222 H 0.6655 1.0361 0.6569 0.0502 1.0000 Uiso R . . . . .
H223 H 0.5733 1.0534 0.5950 0.0478 1.0000 Uiso R . . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.01200(12) 0.01552(12) 0.01341(12) -0.00134(6) 0.00024(6) -0.00014(6)
C11 0.0140(5) 0.0183(5) 0.0154(5) -0.0014(4) 0.0028(4) -0.0028(4)
C12 0.0169(6) 0.0167(5) 0.0107(5) 0.0009(4) 0.0004(4) 0.0005(5)
C13 0.0119(5) 0.0157(5) 0.0148(5) -0.0027(4) -0.0019(4) 0.0000(4)
C14 0.0127(5) 0.0195(5) 0.0132(5) 0.0005(4) 0.0002(4) -0.0016(4)
C21 0.0223(6) 0.0203(7) 0.0204(6) 0.0014(5) 0.0029(4) 0.0014(5)
C22 0.0389(8) 0.0157(7) 0.0391(8) 0.0017(6) 0.0063(6) 0.0002(6)
N11 0.0157(5) 0.0267(6) 0.0155(5) 0.0023(4) -0.0014(4) -0.0034(4)
N12 0.0141(5) 0.0233(5) 0.0153(5) 0.0018(4) 0.0005(4) -0.0009(4)
N13 0.0147(4) 0.0207(5) 0.0153(5) 0.0004(4) 0.0003(4) -0.0023(4)
N21 0.0238(6) 0.0173(6) 0.0225(6) -0.0012(4) 0.0026(4) -0.0001(4)

_refine_ls_extinction_method     None
_oxford_refine_ls_scale          3.29(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 . N13 5_554 1.9693(11) yes
Cu1 . N12 8_456 1.9663(11) yes
Cu1 . N11 . 1.9930(11) yes
Cu1 . N21 . 2.0016(13) yes
C11 . C14 . 1.4055(17) yes
C11 . N11 . 1.1532(17) yes
C12 . C14 . 1.4055(17) yes
C12 . N12 . 1.1523(18) yes
C13 . C14 . 1.4043(17) yes
C13 . N13 . 1.1519(17) yes
C21 . C22 . 1.457(2) yes
C21 . N21 . 1.139(2) yes
C22 . H221 . 0.939 no
C22 . H222 . 0.937 no
C22 . H223 . 0.952 no
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N13 5_554 Cu1 . N12 8_456 109.42(4) yes
N13 5_554 Cu1 . N11 . 109.56(4) yes
N12 8_456 Cu1 . N11 . 110.15(4) yes
N13 5_554 Cu1 . N21 . 112.24(5) yes
N12 8_456 Cu1 . N21 . 110.41(5) yes
N11 . Cu1 . N21 . 104.99(5) yes
C14 . C11 . N11 . 177.27(13) yes
C14 . C12 . N12 . 176.99(12) yes
C14 . C13 . N13 . 179.09(12) yes
C11 . C14 . C12 . 117.71(11) yes
C11 . C14 . C13 . 120.92(11) yes
C12 . C14 . C13 . 121.32(11) yes
C22 . C21 . N21 . 179.68(15) yes
C21 . C22 . H221 . 110.1 no
C21 . C22 . H222 . 109.5 no
H221 . C22 . H222 . 111.2 no
C21 . C22 . H223 . 109.4 no
H221 . C22 . H223 . 110.7 no
H222 . C22 . H223 . 105.8 no
C11 . N11 . Cu1 . 172.91(10) yes
C12 . N12 . Cu1 8_556 174.45(11) yes
C13 . N13 . Cu1 5_555 171.85(10) yes
Cu1 . N21 . C21 . 176.07(12) yes


_iucr_refine_instruction_details_constraints 
;
#
# Punched on 16/07/14 at 12:02:10
#
#LIST     12                                                                    
BLOCK SCALE X'S, U'S 
RIDE C   (  22,X'S) H   ( 221,X'S) H   ( 222,X'S) H   ( 223,X'S) 
END                                                                             
;


_iucr_refine_instruction_details_restraints 
;
#
# Punched on 16/07/14 at 12:02:10
#
#LIST     16                                                                    
NO 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
_database_code_depnum_ccdc_archive 'CCDC 1016797'
